Benzenemethanol, 2,6-dichloro- → trans-6-(2,6-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

HRID 905058

반응식

HRID 905058 반응식
[S:1]([O:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]=[CH:15][O:14]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:21]=1[CH2:22][OH:23]>C(OCC)C.O=P(Cl)(Cl)Cl>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:21]=1[CH2:22][O:23][C@@H:15]1[O:14][C@@H:13]([CH2:12][O:11][S:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=2)(=[O:3])=[O:2])[CH2:18][CH2:17][CH2:16]1

참가 물질

5

반응물 2

HCID 27156Benzenemethanol, 2,6-dichloro-HCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

생성물 1

HCID 54030357trans-6-(2,6-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran수율 71.1%

시약·촉매·용매 2

HCID 24813Phosphorus oxychloride촉매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 1.34 g of 2-tosyloxymethyl-3,4-dihydro-2H-pyran and 1.06 g of 2,6-dichlorobenzyl alcohol in 25 ml of diethyl ether was added a catalytic amount (2 drops) of phosphorus oxytrichloride, and then the mixture was stirred at room temperature for 4 days. The colourless crystals which had precipitated were filtered off, giving 1.582 g of trans-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran, melting at 123°-124° C. Triethylamine was then added to the mother liquor and the resulting mixture was evaporated under reduced pressure and the residue purified by column chromatography through silica gel, in essentially the same manner as described in Example 1(a), to give 338 mg of trans-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran and 306 mg of cis-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran.

후처리

  1. customThe colourless crystals which had precipitated
  2. filtrationwere filtered off

출처 및 근거

ORD 기록
ord-89332c3cc6314095a42f066bc7580a28
출처 데이터셋
uspto-grants-1983_12
특허 번호
US04421758

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